Chepstow Vacation Rentals

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Check prices for these dates

In two weeks
Oct 10 - Oct 12
In one month
Oct 24 - Oct 26
In two months
Nov 21 - Nov 23
In three months
Dec 19 - Dec 21

Vacation Rentals in Chepstow

Cedarhaven - 2 King beds! Hot Tub, Gas Fireplace
Outdoor spa tub

Cedarhaven - 2 King beds! Hot Tub, Gas Fireplace

10.0 out of 10, Exceptional, (4)
"top notch host and wonderful accommodations!! we’re looking forward to a repeat stay!"
Cedarhaven - 2 King beds! Hot Tub, Gas Fireplace
Fully Renovated Cottage on Queen, 3min walk from Beach and Downtown Adventures!
Beach nearby, sun loungers, beach towels

Fully Renovated Cottage on Queen, 3min walk from Beach and Downtown Adventures!

9.8 out of 10, Exceptional, (11)
"We really enjoyed our stay. The place was very nice and as advertised. I would recommend! You'll love the location and the host was really great."
Fully Renovated Cottage on Queen, 3min walk from Beach and Downtown Adventures!
Newly Built 3 Bedroom Cottage, Steps to the Beach
Beach

Newly Built 3 Bedroom Cottage, Steps to the Beach

Newly Built 3 Bedroom Cottage, Steps to the Beach
Historic 1 Bedroom Beach Loft - Boutique Styled, Beach, Lake, stay Drifter Lofts
Terrace/patio

Historic 1 Bedroom Beach Loft - Boutique Styled, Beach, Lake, stay Drifter Lofts

10.0 out of 10, Exceptional, (13)
"Another amazing stay! Cleanliness, quality, design, location all make it the best rental in the area. "
Historic 1 Bedroom Beach Loft - Boutique Styled, Beach, Lake, stay Drifter Lofts
Secluded 3 bedroom bungalow on the Saugeen River with 85-acres.
Interior

Secluded 3 bedroom bungalow on the Saugeen River with 85-acres.

9.8 out of 10, Exceptional, (22)
"This was a peaceful and private location with a view of the river. Amazing sunrise view every morning from the kitchen table. Really enjoyed our stay. Mark was a great host."
Secluded 3 bedroom bungalow on the Saugeen River with 85-acres.
Waterfront Bliss: Firepit & BBQ Cottage R
Outdoor dining

Waterfront Bliss: Firepit & BBQ Cottage R

8.0 out of 10, Very Good, (4)
"Clean and comfortable cottage. It was unfortunate that we could not use the paddleboards or kayaks as the water was quite murky, so we didn't want to swim in it, but we would have liked to be on the water. We chose this cottage specifically because we thought we would be able to access the lake. "
Waterfront Bliss: Firepit & BBQ Cottage R
One-of-a-kind cottage steps from Lake Huron!
Beach nearby

One-of-a-kind cottage steps from Lake Huron!

10.0 out of 10, Exceptional, (16)
"This property is amazing with everything you need to relax and enjoy the scenery,beach and incredible sunset,can’t wait to go back,"
One-of-a-kind cottage steps from Lake Huron!
Stoney Island Sunsets. Blue Nugget is located on the sandy shores of Lake Huron.
Property grounds

Stoney Island Sunsets. Blue Nugget is located on the sandy shores of Lake Huron.

10.0 out of 10, Exceptional, (10)
"Beautiful view of the lake. The cottage is perfect for a weekend getaway. The owners are kind and attentive, the place in clean, comfortable and quiet. My wife and i enjoyed our stay 10/10 would definitely rent again"
Stoney Island Sunsets. Blue Nugget is located on the sandy shores of Lake Huron.
Historic 2 Bedroom Beach Lofts - Boutique Styled, Beach, Lake, stay Drifter Loft
Terrace/patio

Historic 2 Bedroom Beach Lofts - Boutique Styled, Beach, Lake, stay Drifter Loft

10.0 out of 10, Exceptional, (4)
"Apartment was bright and very clean and close to everything including the venues for the Scottish Festival. "
Historic 2 Bedroom Beach Lofts - Boutique Styled, Beach, Lake, stay Drifter Loft
Two bedroom river side apartment with large private yard
Fridge, microwave, oven, stovetop

Two bedroom river side apartment with large private yard

10.0 out of 10, Exceptional, (7)
"Great property with all you would need. Quiet and peaceful along the river. "
Two bedroom river side apartment with large private yard
Scenic Waterfront Cottage Retreat - Firepit & BBQ
TV, fireplace

Scenic Waterfront Cottage Retreat - Firepit & BBQ

10.0 out of 10, Exceptional, (1)
"Great location and quiet area"
Scenic Waterfront Cottage Retreat - Firepit & BBQ
Escape the city and enjoy beautiful, Lake Huron sunsets!
Terrace/patio

Escape the city and enjoy beautiful, Lake Huron sunsets!

10.0 out of 10, Exceptional, (7)
"The cottage was super cute and cozy, we enjoyed the view of the lake and our comfortable sleeps. Would llove to come back for another stay!"
Escape the city and enjoy beautiful, Lake Huron sunsets!
"stunning Serenity Cove On The Lake Cozy Cottage"
House, 2 Bedrooms, Patio, Lake View | Exterior

"stunning Serenity Cove On The Lake Cozy Cottage"

2.0 star property
"stunning Serenity Cove On The Lake Cozy Cottage"
Relaxing retreat with active options: Modern Bungalow near trails and park
Fridge, microwave, oven, stovetop

Relaxing retreat with active options: Modern Bungalow near trails and park

10.0 out of 10, Exceptional, (2)
"Great location."
Relaxing retreat with active options: Modern Bungalow near trails and park
Twilight Haven – Where Family Fun Meets Lake Life
Beach nearby

Twilight Haven – Where Family Fun Meets Lake Life

10.0 out of 10, Exceptional, (3)
"Great location. Walking distance to the beach. Loved the decor. Clean and welcoming. Responsive host. Had a terrific time and plan to book again for next year. "
Twilight Haven – Where Family Fun Meets Lake Life
The GOAT Lakehouse
Interior

The GOAT Lakehouse

The GOAT Lakehouse
Cottage Rental close to lake Huron beach!
Beach nearby, sun loungers, beach towels

Cottage Rental close to lake Huron beach!

Cottage Rental close to lake Huron beach!
In-Town Cottage Near the Beach!
Interior

In-Town Cottage Near the Beach!

In-Town Cottage Near the Beach!
Beautiful, 3 bedroom cottage makes the perfect family getaway.
Private kitchen

Beautiful, 3 bedroom cottage makes the perfect family getaway.

Beautiful, 3 bedroom cottage makes the perfect family getaway.
Fully Furnished House for rent in Kincardine Sept 1st, 2025-June 26th, 2026
Beach

Fully Furnished House for rent in Kincardine Sept 1st, 2025-June 26th, 2026

Fully Furnished House for rent in Kincardine Sept 1st, 2025-June 26th, 2026
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Chepstow Hotel Reviews

Grey Rose Suites

Grey Rose Suites

10/10 Excellent
"Beautiful rooms."
Joanne 4-night trip
Posted 2 days ago
Grey Rose Suites

Find out more about Chepstow

Find out more about Chepstow

Search for holiday rentals in Chepstow on Expedia! You can easily find your home rentals, villas, holiday apartments in Chepstow using one of the methods below:

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Look no further and take a look at our great range of rental properties in Chepstow!

Frequently asked questions

Can I find vacation rentals in Chepstow?

Yes, we offer vacation rentals near top local attractions in Chepstow, or you can choose a secluded option if you're looking for a relaxing stay. Chepstow is known for its local tours.

What are some of the best vacation rentals in Chepstow?

Secluded 3 bedroom bungalow on the Saugeen River with 85-acres.: This vacation home rental outside of Chepstow is located on a river and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a fridge, a stovetop, and a microwave, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

What’s there to see and do in Chepstow?

While exploring the area, visit family-friendly sights like The Huron-Kinloss Ice Cream Trail, or get outside and enjoy nature at Marl Lake. Bruce County Public Library - Cargill Branch and Walkerton Golf & Curling Club are a couple of places you'll find in the larger area.

What’s a vacation rental in Chepstow like?

Vacation rentals are private properties you can stay in for a couple of days or more in Chepstow. Vacation rentals offer extras such as patios, hot tubs, and fire pits so your stay will be comfortable. If you're concerned about a sanitized environment, vacation rentals can provide a sense of safety away from public hotel elevators and lobbies packed with people while still allowing you the enjoyment of travel. You'll also have more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is an attractive option for family trips.